Details
Stereochemistry | RACEMIC |
Molecular Formula | C17H26N4O3S2 |
Molecular Weight | 398.543 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C\C(N(CC1=C(N)N=C(C)N=C1)C=O)=C(\CCO)SSCC2CCCO2
InChI
InChIKey=JTLXCMOFVBXEKD-FOWTUZBSSA-N
InChI=1S/C17H26N4O3S2/c1-12(16(5-6-22)26-25-10-15-4-3-7-24-15)21(11-23)9-14-8-19-13(2)20-17(14)18/h8,11,15,22H,3-7,9-10H2,1-2H3,(H2,18,19,20)/b16-12+
Fursultiamine, also known as thiamine tetrahydrofurfuryl disulfide (TTFD) is an oral FDA- approved thiamine derivative for treating vitamin B1 deficiency and is very rapidly metabolized into thiamine. Fursultiamine possesses a mild beneficial effect in patients with Alzheimer's disease. The improvement could be observed not only in their emotional or other mental symptoms but also in intellectual function. Only mildly impaired subjects showed cognitive improvement. In addition was shown, that fursultiamine have a beneficial clinical effect on some autistic children. Some relatively recent experiments have revealed that fursultiamine was a unique antagonist of hepcidin in vitro that could serve as a template for the development of drug candidates that inhibit the hepcidin-ferroportin interaction. This inhibition is a key for the treatment of anemia of inflammation (AI), a common in patients with infection, autoimmune diseases, cancer, and chronic kidney disease.
Originator
Approval Year
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8120670
Single administration of 100 mg of thiamin tetrahydrofurfuryl disulfide
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23292796
To explore new therapeutic options for Anemia of inflammation (AI) and other iron-related disorders caused by hepcidin excess, there was developed a cell-based screen to identify hepcidin antagonists. Of the 70,000 small molecules in the library, it was identified 14 compounds that antagonized the hepcidin effect on ferroportin. One of these was fursultiamine. To fully characterize fursultiamine as a hepcidin antagonist, there was examined its dose-dependent effect on cellular iron export. Fpn-GFP cells were treated with 100 ng/ml hepcidin and 0–50 μM fursultiamine for 24 hours, and intracellular ferritin concentration was determined. Fursultiamine reversed the effect of hepcidin on ferritin levels, with the IC50 dose in the submicromolar range.
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DSLD |
3907 (Number of products:11)
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1259
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CHEMBL1740659
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3002119
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C1505
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CONCEPT | Dietary Supplement | ||
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DTXSID0023084
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4604
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SUB07852MIG
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C121852
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Fursultiamine
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05J61265PX
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100000084485
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05J61265PX
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804-30-8
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212-357-1
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m5610
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DB08966
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2311
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)